Hydrochloric Acid → HCID 10269594, compound

HRID 586619Notes

Reaction equation

HRID 586619 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)=[C:10]3[N:14]([C:15]=2C(OC)=O)[CH2:13][CH2:12][CH2:11]3)=[CH:4][CH:3]=1.[OH-].[K+].Cl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)=[C:10]3[N:14]([CH:15]=2)[CH2:13][CH2:12][CH2:11]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22335621HCID 22335621, compound

Product 1

HCID 10269594HCID 10269594, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-(4-fluorophenyl)-1-(4-methylsulphonylphenyl)-6,7-dihydro-5H-pyrrolizine-3-carboxylate (0.4 g, 0.96 mmol) is heated under reflux for 1 h in methanolic KOH (2 N, 9 ml, 1.01 g of KOH, 18 mmol). After cooling, water (20 ml) is added and the alkaline phase is rendered weakly acidic (pH 3) using HCl (conc. 25%). The deposited substance is extracted with ethyl acetate, and the ethyl acetate extract is dried using Na2SO4 sicc. and concentrated after filtering. After the removal of the solvent in vacuo, 0.4 g (75% GC) of residue remains. The CC purification is carried out on SiO2 using ethyl acetate as an eluent. The main fractions are concentrated in vacuo and the residue is recrystallized from diisopropyl ether:

Workup

  1. temperatureAfter cooling
  2. extractionThe deposited substance is extracted with ethyl acetate
  3. extractionthe ethyl acetate extract
  4. customis dried
  5. concentrationand concentrated
  6. filtrationafter filtering
  7. customAfter the removal of the solvent in vacuo, 0.4 g (75% GC) of residue
  8. customThe CC purification
  9. concentrationThe main fractions are concentrated in vacuo
  10. customthe residue is recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-5867c3c42b8542a8be050dc260a05d79
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

Loading…